


James & Butch

by aerin_sometimes



Category: Pocket Monsters | Pokemon (Anime)
Genre: Alternate Universe - Canon Divergence, Crossdressing, Cute, Disguise, Gen, Makeover, Short & Sweet, Short One Shot
Language: English
Status: Completed
Published: 2020-06-26
Updated: 2020-06-26
Packaged: 2021-03-03 18:54:38
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,919
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24920386
Author URL: https://archiveofourown.org/users/aerin_sometimes/pseuds/aerin_sometimes
Summary: Inspired by some fan-art by @gi_xxy on twitter of James making up Butch to cosplay as a Sailor Scout.  What if Butch had been James's partner instead of Jessie?  James convincing Butch to crossdress for a disguise
Relationships: Kojirou | James/Kosaburou | Butch
Kudos: 15





	James & Butch

“Are you sure this is the only way?” Butch groaned for what seemed like the thousandth time. The job was fairly straightforward; a public event put on by the management, and held on the rooftop garden, of the Celadon City department store, during which time attendees and their Pokémon would be encouraged to meet, mingle, and enjoy a relaxing afternoon with the bustle of the city far below them; and maybe spend a bit of cash at the shops while they’re at it.

“It’s the only way that doesn’t completely blow our budget for this mission for something like explosives or sleeping gas. Thankfully I have a few connections in town so we shouldn’t need to break the bank.” James replied, knowing that this wasn’t necessarily truthful, but he would never pass up an opportunity for a good disguise, or one that would give him the opportunity to tease Butch a little bit.

The two had been working together for a bit over a month. The two had gone through the Team Rocket training academy with different partners; James with the fiery redhead, Jessie, and Butch with the much cooler and more collected Cassidy. However due to circumstances unknown to them, when they had graduated the academy and were given their official team assignments, Butch and James were paired together, separating them from the people they had grown closest to in their time at the academy. They now find themselves in a hotel room near the department store to make preparations for the mission.

James’s plan was fairly simple, the two would disguise themselves as beautiful women to more easily blend in with the other attendees, identify high value target Pokémon, and distract their trainers while the third pillar of their team, a wise-talking Meowth that had developed the ability to converse with humans, would lure them away, down the back staircase, to the awaiting escape truck loaded with a number of cages. Meowth was currently scouting the location and getting the truck into position.

“But why do we have to go in as women,” Butch probed. “It’s not like anyone there knows what we look like. Why can’t we just go in in normal street clothes?”

“It’s simple psychology,” James mused as he opened a case containing a myriad of bottles, brushes, and powders. “People are generally more likely to let their guard down around women, and less likely to see them as a threat. My plan is just to use those preconceptions against them.”

“I mean, I guess I see what you mean, but how can you be so sure we’ll be able to pull it off? Last I checked neither of us looked particularly girly.”

“Oh Biff, honey, are you doubting your own partner’s skills? I wouldn’t have suggested this plan if I didn’t think we could pass undetected. Now I need you to take your shirt off and come sit in this chair.” James gestured to the swiveling chair set up in front of an illuminated mirror.

“DAMMIT FOR THE LAST TIME, IT’S BUTCH!” he exclaimed. Unfortunately, he knew that was exactly the reaction James was looking for. He seemed to find it funny to see Butch flustered. “Ugh, fine,” he said reluctantly, as he removed his shirt and approached the plush looking makeup chair.

James draped a cape over him and got to work. “Now let’s see what we’re working with here… You’ve got a pretty cute face now that I see you up close. Nothing too pronounced, soft skin, little to no blemishes. This should be easier than I thought! Now pay attention because eventually you’ll have to learn to do this for yourself. Can’t waste time doing the work for both of us forever. We shouldn’t need much in the way of concealer, just a little spot here and there. Your complexion is pretty even so just a light layer of foundation. You’ve got nice, long lashes so we shouldn’t need fake ones, just some mascara and a bit of eyeliner.” Butch hated to admit to himself that this whole process actually didn’t feel half bad. “Eye shadow, a bit of color for your cheeks, and just a touch of lip gloss… okay, looking good! Now just to do something about your hair. It looks pretty good at this length, I should just be able to shift the part a bit to the right, your left, tease out the bangs a little bit… and _voila!”_ James finished as he spun the chair around with a flourish, revealing his handiwork to a visibly stunned Butch. 

“Wha- that’s me?” Butch stammered, in shock at what stared back at him in the mirror. It still looked like him, but… softer, his eyes seemed to be more pronounced and brighter. It was almost as if he was staring at a long-lost twin sister.

“Now then, no time for gawking. First one’s free but next time I’ll coach you through doing it yourself so I hope you remembered the steps,” James said with a wink and a sly smile. “The event is in the afternoon so I gave you a pretty casual, daytime look with a more natural style of makeup. The outfit I’ve picked out should pair perfectly. Light, summery, and should do a good job of showing off those legs. The only reason they’ll have to look twice at you is if they’re checking you out.” Butch visibly recoiled at the thought. The last thing he wanted to happen was for some random guy to try and hit on him. “Now go on and get dressed, here’s your outfit. I’ll be ready in two shakes.” James pushed a garment bag in to his hands as Butch turned and left the bathroom.

Now it was time to see what was in store for him in the way of clothes. It started simple enough, a dark red sleeveless top, that upon closer inspection, matched the color of his eyes fairly closely, and a pair of distressed jean shorts, a little short for his liking, looked like they would only cover down to the middle of his thigh. But he was in no position to argue, there were only a couple hours left before the event was scheduled to start. The shoes, what appeared to be normal sneakers at first glance, actually had about a three-inch wedge built in, which would serve to bring up his height a little bit, as well as to accentuate the tone of his legs. James did say that was the focus after all.

As Butch removed the final articles from the bag, he felt his stomach sink. There was a bra, basic black, with what felt like slightly firmer water balloons stitched in to the cups, seemingly custom made for this purpose, then finally _two_ pairs of panties, women’s underwear. One he would come to learn, a bikini cut, the other, a thong that was slightly smaller, and also had a more rigid front panel.

“Why the hell do we have to wear women’s underwear too?!? And why are there two pairs?” He shouted to James

“Well your normal boxers would show through the shorts of course, wouldn’t be a very flattering look,” James replied casually. “As for why there are two pair, the smaller pair is there to keep your little ‘Buzz’ from making a special appearance while we’re incognito. This is honestly ‘The Art of Disguise 101’. I trust you can figure out how to situate everything. If you can’t get the bra, just hook it in the front then swivel it around.”

Butch never imagined in his training days part of the job would be discussing how to put on a bra and panties with another guy, but this was for the job, so he soldiered on. The first pair of panties were definitely a bit tight, but with a bit of pulling and tucking, he was able to situate everything so he wouldn’t have an unwanted guest during the event. Everything else went on without much issue, he didn’t even really struggle with the bra. Finally came the shoes, which went on fairly easily, but then, the first steps, the moment of truth. He could feel his legs shake slightly as he stood up. It was obvious from the start that his normal gait would not do.

“Having a bit of trouble?” James mused as he emerged from the bathroom, “Well they’re wedges so it shouldn’t be quite as hard, but just try not to overthink it. Just straighten your back, as you take a step, put your weight first on your heel, then shift forward to the toe, and just put one foot straight in front of the other. Just try and walk over to me.”

“Okay, I can do this, it’s only a few feet,” Butch said as he exhaled. He couldn’t take his eyes off his feet. He had to get the motion down just right. Heel-toe, heel-toe. After a couple steps, they started to become more fluid, his mincing walk becoming more of a confident stride. He took a couple laps back and forth, thoroughly pleased with himself that he was able to conquer this mountain so quickly.

“Well it seems like you’ve got the hang of it now, why don’t you try and lift your head up,” James remarked. Butch’s eyes had been trained on his toes the entire time, he realized James had been out of the bathroom for some time and he hadn’t even had a look at his partner’s disguise.

James’s makeup was similar to his own, understated, but still noticeable, and perfectly accentuated his natural features. As for his hair, it looked as though he had clipped on a set of wavy, shoulder-length extensions that perfectly matched his unique, periwinkle hair color; quite a feat really. He was wearing a simple white, or maybe very light pink, dress that went down to about his knees, paired with a strappy pair of nude heeled sandals.

James clapped lightly, “I’d say we’re just about ready, wouldn’t you? Now we can’t exactly go around calling you Butch, now can we. I usually go with Jamie… Oh, I know, how about we keep it simple and just go with Brie?”

Brie… Brie… Brie…

Butch… didn’t hate it surprisingly. It was simple, easy to remember, really fit all the criteria for a good code name. Jamie would be easy to remember as well since it was so close to James. “Yeah, Brie works just fine”

“Now then, the last thing to do is something about your voice. It would be a dead giveaway as is. Normally it takes a bit of training to get a good feminine voice but since we’re on short notice, we should be able to get you to a point where you can pass as just having a slight cold. Try and speak a bit softer. Shift your pitch up just a bit, and exhale more as you speak.”

“How’s this?” It was still distinctly Butch speaking, raspy tone and all, but there was also a gentler quality to it, less abrasive. Not perfect, but as James had said, it would do in a pinch.

“Now then Brie, I think it’s about time we head to the department store. I’m sure we’ll be able to find some great deals.” Jamie said with one final wink.

“Sounds great Jamie. Let’s get going!”

Brie could definitely see herself enjoying this sort of disguise in the future, but only for work, of course.

**Author's Note:**

> TBH I read a lot of online crossdressing-related short stories as a pre-teen so there's probably some real cliche stuff in here that I subconsciously picked up from that. Thanks for reading!


End file.
